Synthetic method for cyclohexylamine

A synthesis method and technology of cyclohexylamine, applied in the preparation of nitrogen-oxygen/nitrogen-nitrogen bonds, organic chemistry, etc., can solve problems such as difficult operation, high production cost, and difficult application, and achieve mild reaction conditions and low production cost. The effect of low, high product purity

Inactive Publication Date: 2009-08-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reducing agent itself is expensive, difficult to operate, high in production requirements, and high in production costs
[0005] (3), document J.Ind.Chem.Soc., 68(2), 95-7; 1991, the electrochemical method uses hydrochloric acid as the reaction solvent to realize the above process, but the electrochemical method has higher requirements on the reactor and serious pollution ,higher cost
[0006] (4), document Chem.&Ind.1971(8), 227-8 uses aluminum hydride of magnesium to realize the reduction of cyclohexanone oxime, but the catalyst itself is difficult to synthesize and difficult to apply
However, the catalysts for these methods are expensive and difficult to use

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Embodiment 1: a kind of synthetic method of cyclohexylamine, carries out following steps successively:

[0013] 1. Prepare a fresh Raney nickel (Raney Ni) catalyst (this is the prior art): 2g Ni-Al alloy is dissolved in 100mL sodium hydroxide aqueous solution containing 10g sodium hydroxide in batches until no bubbles are produced. Pour off the upper aqueous solution, wash with fresh distilled water several times, until the final wash is neutral.

[0014] 2. In a 500mL autoclave, 80mL (62.32g / 0.74mol) of cyclohexane was added sequentially, and all the above-prepared Raney

[0015] Ni and cyclohexanone oxime 113.2g (1.0mol). First replace the autoclave with hydrogen three times, and then fill it up to 3.0 MPa; then add 17 g (1.0 mol) of ammonia into the autoclave. Heat the above-mentioned mixture in the autoclave to 100°C for reduction reaction. During the reaction, the pressure drops, and hydrogen needs to be continuously replenished. Keep the pressure at 3.0MPa for h...

Embodiment 2

[0019] Embodiment 2: a kind of synthetic method of cyclohexylamine, carries out following steps successively:

[0020] 1, prepare fresh RaneyNi catalyst: with embodiment 1.

[0021] 2. In a 500mL autoclave, add water 100mL (100g / 5.56mol) and RaneyNi catalyst 3.0g (composed of 1.0g of fresh Raney Ni catalyst and 2.0g of Raney Ni catalyst in the filter cake recycled in Example 1) and 226.4 g (2.0 mol) of cyclohexanone oxime. Replace the autoclave twice with hydrogen, then fill it up to 1.0MPa, heat the above mixture in the autoclave to 150°C for reduction reaction, the pressure drops during the reaction, hydrogen needs to be continuously replenished, and hydrogenation is carried out under the condition of maintaining the pressure at 1.0MPa ; Until the hydrogen is no longer absorbed, the pressure is kept constant at this time, and the reaction time is 28h in total.

[0022] 3, with embodiment 1. The resulting cyclohexylamine yield reaches 55.7%. The total yield of the obtaine...

Embodiment 3

[0023] Embodiment 3: a kind of synthetic method of cyclohexylamine, carries out following steps successively:

[0024] 1, prepare fresh RaneyNi catalyst: with embodiment 1.

[0025] 2. Add 79.2 g (2.47 mol) of methanol, 10 g of fresh Raney Ni catalyst and 113.2 g (1.0 mol) of cyclohexanone oxime in sequence into a 500 mL autoclave. The autoclave was first replaced twice with hydrogen, and then filled to 5.0 MPa; and 17 g (1.0 mol) of liquid ammonia was added to the autoclave. Heat the above-mentioned mixture in the autoclave to 60°C for reduction reaction. During the reaction, the pressure drops, and hydrogen needs to be continuously replenished. Keep the pressure at 5.0MPa and hydrogenate; until no more hydrogen is absorbed, the pressure remains constant at this time, and the reaction time A total of 7h.

[0026] 3, with embodiment 1. The resulting cyclohexylamine yield reached 83.2%. The total yield of the obtained cyclohexylamine and dicyclohexylamine was 91.5%.

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Abstract

The process of synthesizing cyclohexylamine includes the reduction reaction of butanone oxime and hydrogen inside solvent with ammonia at pressure of 1-5 MPa and temperature of 20-150 deg.c in the presence of Raney Ni catalyst; and the dewatering, drying and rectification of the reaction product. The Raney Ni catalyst amount is 0.3-10 wt% of butanone oxime, and the weight ratio between ammonia and butanone oxime is 0-1 to 1. The cyclohexylamine synthesizing process has low cost and high yield.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing a chemical intermediate—cyclohexylamine. Background technique [0002] Cyclohexylamine is an important organic chemical intermediate. Its synthesis methods mainly include catalytic hydrogenation of aniline, gas-phase ammoniation of cyclohexanol and catalytic ammonolysis of cyclohexanone. Higher requirements. And for the enterprises with advantages of raw materials of cyclohexanone oxime, using cheap cyclohexanone oxime to produce cyclohexylamine is also a promising method. At present, by cyclohexanone oxime as raw material synthesis cyclohexylamine mainly has the following several research reports: [0003] (1), literature Syn.Com., 34 (4): 599~605, J.Chem.Res., syn., 2003 (3): 332~334 and J.Chem.Res., syn.1998 (3 ): 160-161, using ammonium bicarbonate to react with cyclohexanone oxime under the catalysis of metal magnesium, zinc or palla...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/40C07C211/35
Inventor 陈新志刘金强钱超
Owner ZHEJIANG UNIV
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